Tetrahydrofuran → 3-Ethynylpyridin-2-amine

HRID 1927208Notes

Reaction equation

HRID 1927208 reaction equation
C1COCC1.C[Si]([C:10]#[C:11][C:12]1[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][CH:17]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:11]([C:12]1[C:13]([NH2:18])=[N:14][CH:15]=[CH:16][CH:17]=1)#[CH:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 574756663-((Trimethylsilyl)ethynyl)pyridin-2-amine

Product 1

HCID 124225263-Ethynylpyridin-2-amineYield 62.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a THF (120 mL) solution of 3-trimethylsilanylethynyl-pyridin-2-ylamine (5.9 g) described in Manufacturing Example 1-1 was added tetrabutylammonium fluoride (34 mL: 1M THF solution) at 0° C., which was stirred for 25 minutes at room temperature. Water was added at 0° C. to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate, and filtered, after which the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=1:1) to obtain the titled compound (2.3 g).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationafter which the filtrate was concentrated under a reduced pressure
  6. customThe residue was purified by silica gel chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ca4fa9398d7648a6b032499922db0b0e
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

Loading…